New Perspective for Natural Products Synthesis: Concise Synthesis of (+)-Sch 642305 by Chiral Auxiliary Multiuse Methodology

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• 作者：Hiromichi Fujioka ; Yusuke Ohba ; Kenji Nakahara ; Mayuko Takatsuji ; Kenichi Murai ; Motoki Ito ; Yasuyuki Kita
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：December 20, 2007
• 年：2007
• 卷：9
• 期：26
• 页码：5605 - 5608
• 全文大小：78K
• 年卷期：v.9,no.26(December 20, 2007)
• ISSN：1523-7052

文摘

The synthesis of (+)-Sch 642305 is an example of chiral auxiliary multiuse methodology, which shows a new perspective for the synthesisof compounds with multiple asymmetric centers. Thus, (+)-Sch 642305 was concisely synthesized from the known compound. Every reactionis stereoselective, and the chiral nonracemic hydrobenzoin worked as chiral auxiliary for desymmetrization of diene, as a template for attainingregio- and stereoselective reactions, as an oxygen source at the C4-position, and as a protecting group of hydroxyl functions. Namely, thechiral auxiliary played a role in every step throughout the synthesis. Furthermore, the synthesis contains a new protocol for obtaining '-alkylated enone compounds.